10 Years Ago Today

Ten years ago today, I had one of my best Halloween experiences going to work en femme. I documented that day with a “live blog,” that is, I added to my Halloween blog post throughout the day as things happened (or did not happen). Here is a repost of that wonderful day.

8:03 AM Post:

Up at 5 AM. Took care of the menagerie and began the transformation at 5:35

I took my time doing my makeup (slow, but steady), so it took a little longer getting ready.

Out the door at 7:05 and I arrived at work at 7:40.

Although I only mentioned that I would be a woman at work to my boss, no one is surprised and expected me to do it.

8:30 AM Post:

When I walked in the building this morning, I asked our receptionist to take some photos. Here is one:

8:45 AM Post:

Three people noticed that I am wearing a new wig!

8:48 AM Post:

The receptionist just called me “Staci,” which is the name I used before switching to Stana. She also asked me how I tied my scarf and I gladly showed her.

9:15 AM Post:

There is a bit of a lull here, so here is another photo (sans glasses and cape) taken by the guy who sits in a cube adjacent to me. Instead of an iPhone, he used a Canon digital SLR camera.

10:05 AM Post:

I just attended a “gemba” (reps from various departments stand in a circle and update the group about the status of a project). The Director of Engineering ran this gemba and called me “Caitlyn.” He is always impressed with my “costume” and was impressed again this year.

A few other people did wear costumes today. 

10:20 AM Post:

A number of women complimented me on my outfit and they love my shoes (I do, too)! They are also amazed on how well I navigate in them... just like a woman.

I bought these shoes from Nine West two years ago, but I never had the opportunity to wear them until now because I did not have an outfit that went with them.

So far, they have been very comfortable despite their 4-inch heel.

11:05 AM Post:

Going to Dress Barn in a little while. The sales associates wanted to see how the dress they sold me on Monday looks on me today.

12:35 PM Post:

I went to Dress Barn and the sales associates who sold me the dress on Monday were not in the store; they work later in the day today.

Not to waste a Dress Barn visit, I browsed the racks and took a half dozen items to the dressing room. Some things looked and fit better than others. 

One dress fit perfectly and looked great: a simple figure-hugging black sheath dress with a gold front zipper that makes the dress. I bought the dress and returned to work.

1:00 PM Post:

As I got ready to leave Dress Barn, my feet started complaining loudly and when I got to my car, I switched to my black medium height wedges. 

1:15 PM Post:

Another lull, so it is time for another photo. My boss' boss took this one on her iPhone as I stood in her office doorway. 

1:53 PM Post:

It is very quiet here. Friday afternoon and things are winding down.

I am very tired. I went to bed late watching the Patriots, got up early to femulate and did not sleep that well in-between because I was excited about today. 

One of my biggest fans here just stopped in to ask me how it is going. He goes out of his way to use the proper pronouns when I am a woman and he once said that I missed my calling and should have been a professional female impersonator.

2:50 PM Post:

This will probably be my last live post for awhile because I am leaving work and going to the mall to shop for a new evening gown. My next post will probably be from home this evening.

7:30 PM Post:

I was successful at Macy's at the mall. I bought a Connected sequin-lace cowl-neck sheath in purple. The photo on the website does not do the dress justice; the sequin is not apparent in the photo, but it makes the dress in person.

My feet had recovered by the time I arrived at the mall and I switched back to heels for my mall tour.

I am going to bed early tonight. I am exhausted!

∞ ∞ ∞

The day-after post was an addendum to my live blog post, so in order to tell the whole story here it is.

I received a lot of positive comments about doing the live blog on Friday and plan to do it again if the opportunity arises and it makes sense to do it. Internet access is the key to doing it successfully, so doing it at work was a perfect scenario.

∞ ∞ ∞

Most of the live blog posts were short and I want to expand on what I wrote on Friday, so here goes!

∞ ∞ ∞

In the 10:05 AM Post, I mentioned attending a “gemba.”  When it was my turn to speak, I said “I had nothing” because I had no news regarding my part of the project under discussion. 

The moderator of the gemba, our Director of Engineering, asked me, “Are you sure there’s nothing you want to add?” 

Knowing him as long as I have, I am sure he was teasing me about my “costume.”

Anyway, after a long pause, I said, “No,” but after I thought about it, I wish I had said, “I guess you all figured out by now that I am transgender.” 

That would have been a gemba they would be talking about for years to come!

∞ ∞ ∞

When I went to show myself to my boss, I found her in her boss’s office (my boss and her boss are women and both know I am transgender, but now that I think about it, I bet that they don’t know that the other one knows because I came out to them separately).

Anyway, they were both wild about my “costume” and my boss’s boss blurted out, “You look better than (my boss)!”

I did not notice my boss’s reaction, but I think my boss’s boss might regret what she said. 

The truth is that although my boss is pretty and is about 10 years younger, I think I can modestly say that I compare favorably to her as a woman.

∞ ∞ ∞

Friday as a woman was more like two days as a woman: a day as a woman at work and a day as a woman outside of work.

Outside work, I felt like an invisible woman passing unnoticed among the civilians. When I interfaced with civilians like the sales associates at Dress Barn and Macy's, they treated me like a female customer. I sometimes suspect and detect that such treatment is due to the $ in the word cu$tomer, but on Friday I think the treatment was genuine. At least it appeared genuine to me and that is what counts.

At work, everyone knows me as a guy the rest of the work year who does a good job looking like a woman one day of the year. Five co-workers know what's really up, but I don't know what the other 70 people think.

Comments like “you look too good” or “you do it too well” infer that they suspect something is going on beyond a Halloween costume. And those are just the folks like our CEO on Friday, who are vocal to my face about it. Others probably have similar opinions, but keep their thoughts to themselves or amongst themselves.

Whatever their thoughts, they all seem fine with me. I have an excellent relationship with everyone in my office and that probably has made it easier for them to accept me (or put up with me) during my one day per year fling as a woman.

So why do I do it?

Of course, I love doing it, but there is a small ray of hope that someday I will be able to go to work (and go everywhere else) as a woman all the time. My Halloween fling is a test for me and my co-workers for when that wonderful day finally arrives and I think we all passed. 

Wearing Boston Proper

Dick Wesson femulating in the 1953 film Calamity Jane.

Halloween Eve

Wearing Trina Turk

Bruce Mars, Noam Pitlik, Joseph V. Perry and Dick Wesson femulating on television’s That Girl.

Tami Visits Frederick’s

Tami’s Adventures in Crossdressing, Part 3

By Tami

In Part 1, I described a bit about myself and how Femulate’s hostess, Stana, and I share some similarities; first and foremost, our love of crossdressing. In Part 2, I related how as a very young boy, I got hooked on crossdressing when I hooked up the clasps of bras and garter belts and donned a wide variety of wondrous female attire owned by my mother and two older sisters.  

After those first young steps in spiky heels, I matured into a typical adolescent American male and turned my attention to the traditional wearers of soft, sensual attire – girls. The pursuit of the so-called fairer sex and a busy life of school, socializing and sports kept me too busy to don anything other than traditional male clothing. I never crossdressed during my high school and college years. 

After college I got married and started having kids. Crossdressing gradually became a distant memory, but I never completely forgot those daring, secret adventures of my youth, especially when I was looking at the feminine version of myself in a full-length mirror in my sisters’ walk-in closet. I never lost the interest in women’s clothing, but I just hadn’t had any opportunity to try anything on and truth be told, I really didn’t think about it much at all.

As a young crossdresser, I didn’t really understand that I was not alone, but then again, I don’t believe I even considered that others did it. I just knew that I did and that was enough. The idea that I was far from alone would have come as a shock to me in those early years.


From reading many of the comments posted on Femulate, I know that there are many among us who followed the same path – we crossdressed as youngsters, grew out of it during adolescence (mostly due to being too “distracted”) and then rediscovered our secret passion of crossdressing as we grew older.

I didn’t slip back into a silky slip until I was in my thirties. I reconnected to this magical, forbidden “hobby” because I witnessed another crossdresser trying on some distinctly feminine items. On a business trip to Los Angeles, I happened to pass by the world famous Frederick’s of Hollywood lingerie emporium on the equally famous Sunset Strip. As I drove slowly past, I observed window after window displaying mannequins adorned in many of the types of items I occasionally got to wear as a young boy: corsets, bustiers, garter belts, stockings, sheer lacy robes, pretty bras and more. I just had to stop and explore those special windows up close.

Many of you reading this surely understand. You probably furtively stole glances into lingerie store windows or were brave enough to just stop and more closely stare at the appealing displays. Every window that day called to me, saying, “look at all these beautiful things, wouldn’t it feel wonderful to wear them all?” I was more than just interested, I just couldn’t stop myself from actually going into this living museum to statin, lace and leather. It was literally my very first venture into any lingerie store and I found it almost overwhelming. The store was big and busy, lots of females were shopping and working there, from the very young to older ladies, along with some couples and as it turned out, I was not the only solo male looking through the amazing racks of finery. 

I felt empowered when a young sales girl said that if I needed help just ask. I replied that I just wanted to browse for something for my wife, so with a big smile she let me do just that. I excitedly pursued rack after rack of sexy panties, garter belts, corsets, bustiers, slips, petticoats and stockings. 

As I was walking around the store, marveling at the wide variety of wondrous unmentionables, I spied a middle-aged male who was doing something shocking; well, at least shocking to me. He was dressed like any typical male, button front collared man-tailored shirt, slacks held up by a leather belt, no discernible jewelry, but a pretty young sales girl was placing a pair of very high stiletto heels on his feet. As she guided him into a pair of beautiful and sexy open-toe high heels, I observed that his toes were sparkling with bright pink polish, which were visible through very sheer stockings. He was also wearing a sparkly ankle bracelet with a pink heart dangling from it. After stepping into the girly shoes, he would walk around to see how they felt, pulling up his trouser legs so he could see the full effect the heels had on his legs. The sales girl would encourage him by saying how pretty the heels looked on him, how they made his legs look long and sexy and suggesting he should try on the next pair to see how they fit. 

This daring young man in the sky-high heels and the sales girl helping him, seemed to have no problem with what they were doing, nor did any of the other shoppers. Anyone in that area of the large store could not help but notice as he tried on a few pairs of pretty high heels and walked back in forth in them, stopping to see how he looked in the mirrors placed at angles on the floor of the shoe area. 



As I sneaked frequent glances towards this man in stockings and heels, it slowly dawned on me that I was not the only one who wore the apparel of the other sex. Not only were there others, but at least some of them, like this shopper in Frederick’s of Hollywood, did it in public unabashedly. 

When I did it as a youngster I did it in secret and never told a soul. I was fearful that anyone might find out and label me a freak. This fellow shopper, the stores’ all-female staff, and the other customers didn’t react like there was anything at all abnormal going on.



That experience turned out to be an enabler for me for future outings. If some other male could boldly try on high heels and expose his stocking clad legs in a busy, crowded store, who was I not to be equally daring? I didn’t immediately do exactly what he did, but believe me, I really wanted to... and more. I imagined trying on whatever was required to hold up a pair of stockings, plus dresses and skirts and blouses and earrings. 

My imagination started to get way ahead of me. I didn’t graduate to trying on girly-girl clothing in stores until years later, but I was already dreaming of it. I so wanted to be like him – to walk into a store while wearing stockings, and other unmentionables under my male outer clothing and being helped by a sales girl to try on every type of feminine finery imaginable. 

What I did that that day instead was to purchase a darling set of dreamy lingerie for my beautiful wife. Even though her own choices of underthings were not so overtly feminine or sexy as those sold in Frederick’s, she obliged my tastes by occasionally wearing what I bought her on that fateful trip. The gift was composed of a matching set of lacy panties, bra, garter belt and silky sheer stockings. Like most women born in the fifties, she had switched from stockings to pantyhose long before this and found the garter-supported stockings to be old-fashioned and less comfortable. She indulged me by wearing the set I bought her on special occasions. 

And so the pink dye was cast, forgotten unmentionables had slipped back into my house and my life and I was obsessed with the idea of myself dressed in items just like them and more. This opened or reopened a chapter that I thought had closed long ago. It took me places I could not have dreamed of as a young budding crossdresser.



In the Part 4, I will tell you the tale of how I gradually re-entered the world of wearing feminine finery, daringly so, and more and more frequently as the years rolled on.

Wearing Shein

Rachel, a Femulate reader and practitioner

Not So Hot

Zoe is a prolific digital miner and often sends me links to femulating-related videos that she digs up on the Internet. She discovered gold recently when she found a television pilot for the famous femulating film Some Like It Hot.

The television pilot was produced in 1961 by Mirisch Productions (the same producing company behind the original film). The film’s stars, Jack Lemmon and Tony Curtis, made cameo appearances for the pilot, reprising their original characters from the film for the opening scene only. The pilot then shifts to new actors for the main characters: Vic Damone and Dick Patterson (playing the “new” Joe and Jerry). 

The pilot was not picked up as a series; it remained unsold, but you can view it on YouTube by clicking here.

Wearing Shein

Vic Damone femulating in an unsold television pilot for Some Like It Hot.

At Work En Femme

Halloween is “National Crossdresser’s Day,” so they say. I guess there is some truth in that because my first public crossdressed outing was on Halloween and I know many other crossdressers also poked their bewigged heads out of the closet for the first time on October 31. And over the years, I have continued to crossdress on Halloween to attend parties given by friends and COS. But, Halloween 2000 was different. 

One week before Halloween, my company announced that they were sponsoring a day of Halloween events including a costume contest. In all my years of being gainfully employed, no employer of mine had ever sanctioned wearing costumes to work on Halloween. I know some of you have gone to work en femme on Halloween and I often considered it, but I never had the nerve to do it. However, this year, I could go to work en femme with the blessing of the boss! T’was a crossdresser’s dream-come-true.

There was no doubt that my costume would be en femme, but how en femme was the question. I considered my options and decided to dress appropriately for my workplace, which is an office. My costume would be “office girl drag.”

I had a plenty of outfits that qualified as office girl drag, so I went through my stash to decide what to wear. I narrowed my choices down to three outfits. To make the final decision, I slipped into my unmentionables and modeled each outfit. My wife and I agreed that the black print, short-sleeved, knee-length sheath looked best. To round out the ensemble, I chose tan pantyhose and a pair of black patent pumps with 3-1/2-inch spike heels.

The night before Halloween, I prepared for the next day. I depilated, combed out my wig and laid everything out so I could get ready as quickly as possible Halloween morning. I turned in early because I had set the alarm clock for 4:45 AM to give me enough time to depart for work at 7:15 fully made-up and dressed. However, turning in early did no good because I was so excited I had a hard time falling asleep. It was after 2 AM before I finally nodded off and I woke up 15 minutes before the alarm clock was set.

I got up, shaved, showered and applied my makeup. For a change, I made no makeup errors and was finished by 6:15. I put on my undies, dress, shoes and wig, then I checked myself out in a full-length mirror. Was that Nicole Kidman’s reflection in the mirror? Not quite, but when I squinted real hard, I thought I saw Nicole Kidman’s mother.

Last thing to do was my nails. I glued press-on nails to my pinky and ring fingers, then I had an incredibly hard time gluing the nails to my middle fingers. None of the press-ons fit quite right and the glue could not make up the difference. Time was running out, so I decided to forgo the nails. After removing the press-ons from my pinky and ring fingers, I grabbed my purse and hit the pavement.

The commute was uneventful and I arrived at work 15 minutes early. I exited my car and walked to the main entrance enjoying the feminine beat of my heels clicking on the sidewalk.

Inside, the first people I encountered were our receptionist and a woman from Human Resources, who were lining up pumpkins for the carved pumpkin contest. At first neither of them recognized me. Then, they both recognized me and started gushing over my costume. So far, so good.

I went upstairs to my cubicle. Since I was early, there was no one around to see me, so I went to the cubicle of one of my best friends at work (she is one of the few people who gets to work earlier than I). I stuck my head around the corner of her cubicle and said, “Trick or treat.” She was floored!

After she regained her composure, she began calling me “Stella” and insisted on escorting me to the cubicles where other early birds were already at work. Our first stop was her boss, who had been with the company about six months. I don’t work directly with him, but he is only three cubicles away from me and we cross each other’s paths each day. My friend pushed me into his cubicle and he had no clue. At first he thought I was a new female employee, but my friend blew my cover, “Don’t you recognize him?” He didn’t until I explained that I was the guy three cubicles away.

And that was the way it went all day long. A tall woman in a Halloween costume environment is a dead giveaway. As a result, the majority read me as a man in drag, but did not know which man until I showed them the mug shot on my security card. On the other hand, a minority did not read me at all including some folks that I work with on a regular basis.

By mid-morning, the word was out that there was a guy in drag upstairs and a procession of onlooker began marching up to my cubicle to check me out. (No other guys appeared in drag. In fact, only a handful of guys wore costumes at all. On the other hand, the woman had a lot more Halloween spirit and approximately 1 out of 4 women appeared in costume.)

In general, women loved my costume. Some were amazed that I shaved my legs and my arms. Others complimented me on my makeup and some asked, “Did your wife do your makeup?”

“No, I did it myself,” I responded, which caused further amazement.

A few remarked that I should quit my job and become a professional female impersonator! One woman said, “I made her day,” and she returned to my cubicle three times with two or three new onlookers in tow each time. A pretty administrator remarked, “You look better than most women I know.” That made my day!

I don’t think I fooled everyone. A few women gave me knowing looks… like they knew I looked too good to have only done this once. But, I didn’t mind. 

On the male side, the majority appreciated my costume, but there were two or three who seemed to be phobic about it… typical macho twaddle, I guess.

Shortly after getting to work, my pantyhose began running like crazy! I don’t know if they were defective or I was careless, but by 10 AM, I had three runs that were getting bigger by the minute. I wanted to look my best, so I left the building for a few minutes and drove to a nearby CVS to buy a new pair.

Now, this is the scary part because the CVS was not having a Halloween costume contest. I parked the car and walked into the CVS passing a handful of people who paid me no mind. I entered the store and to avoid causing a commotion, I went to the first saleswoman I saw and explained that I ran the pantyhose of my Halloween costume and needed a new pair. 

“Hosiery is in aisle eight, Ma’am,” she replied unfazed by my Halloween costume hint.

I guess I was not going to cause a commotion, so I went to aisle eight, picked out a pair (only $1.99), then I went to the register where the same saleswoman rang me up without a clue.

Now, here is the amazing part. I never used a femme voice. I spoke in my normal male voice, which is admittedly soft-spoken, but definitely male. I guess the saleswoman’s eyes convinced her that I was a woman no matter what clues her ears might be picking up. (I had read about this phenomenon, but did not believe it until I actually experienced it.)

I returned to my office and waited for the results of the costume contest. A lot of people said they would vote for me and I guess they did because I won. I thought there were three or four costumes that were better than mine, but I guess having the guts to wear the costume I wore was that little extra that pushed me over the top.

I felt a little guilty about that because it did not take any guts to do what I did. This was something I wanted to do for a very long time. I also felt like I cheated a little because this wasn’t a costume I put together overnight. I’ve had practice dressing like this for years.

I’ll admit that I did have some qualms about possibly losing the respect of some of my colleagues. But when I thought about it, if somebody lost respect for me because I crossdressed on Halloween, then I don’t want their respect. So, qualms be damned! Tighten that corset as tight as you can. Today you are a woman!

I made one fashion blunder… my choice of footwear. I had not worn that particular pair of high heels in such a long time that I had forgotten why I stopped wearing them. Because they hurt a lot in a very short time! I have other pumps with the same heel height and even higher that don’t hurt like that pair did. The only saving grace is that I did not have to get up and walk around too much. I could just sit at my desk and pose for my admirers whenever they showed up.

However, I regret that I did not wear more comfortable shoes because I wanted to go to the mall, have lunch at the food court and do some window-shopping. But by noon, my feet were so hobbled that walking around the mall would have been very ugly.

I also had a fashion revelation. Wearing a tight corset all day was quite painless. The corset did inhibit movement, but it did not cause any aches or pains (like my shoes and clip-on earrings), while improving my figure immeasurably. 

I had the time of my life. I wished the day would never end, but it did and now I have a lot of wonderful memories about my first day at work en femme.

Wearing Shein

Jordan Peele and Keegan-Michael Key femulating on television’s Key and Peele.

It's That Time of Year

Remembering Fantasia Fair

This week is TransWeek in Provincetown, Massachusetts. Previously known as “Fantasia Fair,” I attended 17 years ago and today's post are my thoughts about that amazing week en femme 24/7 in October 2008.

During my week en femme in Provincetown, I shopped, dined, and had many other encounters with civilians throughout Provincetown and never had a problem. Everyone I encountered was friendly and treated me like a lady with one exception. Twice, I bought items at a pharmacy on Commercial Street.

First time, I found what I wanted to buy and stepped up behind a dude talking to the pharmacist who was standing at the cash register. The dude and pharmacist concluded their chat. I stepped up to the counter and the pharmacist turned his back on me and walked away instead of ringing up my purchase. 

I waited a minute or two for someone to ring me up. A middle-aged woman finally showed up to handle my purchase. She was very cold, avoided eye contact and the only words out of her mouth was the amount of money I had to pay.

Second time, the same woman rang me up with the same level of frigidity.

In both cases, I was my charming self, but the only response I received was a blank cold stare. I would not say that the pharmacy was transphobic, but they certainly were not transfriendly and being the only pharmacy in the center of town, I am sure they made a lot of money off the trans folks visiting town last week. Go figure!

***

I improved and streamlined my makeup skills during the week. Doing my makeup twice a day for a week, I found shortcuts to get the job done more quickly. (“Practice makes perfect.”) By week’s end, I probably shaved 15 to 20 minutes off my normal 1-hour makeup routine. I also was able to experiment with different looks and colors, which was a lot of fun!

***

I learned a lot about woman’s footwear during my week en femme. Downtown Provincetwon uses cobblestones for many of its sidewalks and they are unforgiving when you wear high heels. I quickly learned which shoes to wear when I had a lot of walking to do, that is, my booties and my mid-heel pumps with the chunky heel. If I wanted to wear heels at an event, I carried them with me while walking in my comfortable shoes, then changed to heels when I arrived at the event. Luckily, many events were in my hotel, so I did not have to carry heels around town that often.

***

I had a lot of fun mixing and matching separates (tops, jackets, skirts, pants) to create outfits during the week. (Is it still crossdressing when you wear pants?)

***

I reached a new level at Fantasia Fair. Femulating 24/7 for a solid week, you stop thinking about the fact you are femulating and begin living like a woman. All the techniques you use for femulation become second nature; you no longer have to think about using those techniques because they are now natural. I believe that during Fantasia Fair, I came as close to feeling like a natural woman as I can be and I hope that that second nature will stick with me forever.

***

Will I attend future Fantasia Fairs?

As my euphoria peaked at the end of the week, I told anyone who asked that I would be back next year and that I would begin saving money for the trip on Monday to make next year’s trip possible.

After the banquet Saturday night, I began reconsidering my return next year or any year.

The civilians in Provincetown are aware that the circus is in town, which makes it impossible to pass. Every tall woman is a potential man in a dress, so the civilians check out every tall girl to see if that is the case. I never experienced anything untoward in Provincetown, but being a very tall girl, I became annoyed by the inspection that I (and all the other tall girls) had to undergo every time we walked outside.

If you are a closeted femulator and want to get out of the closet in a safe way, I highly recommend Fantasia Fair to you, but I don’t need that. I could take the money I saved to bankroll a trip to Fantasia Fair and have a wonderful time shopping for a new wardrobe in the malls and outlet stores of Connecticut. Sure some people might gawk at me as I shopped, but most would not because (1) they would not be alerted beforehand that a crossdresser may be in their midst and (2) I often pass and do not attract attention to myself in a bad way, that is, in a way that gives away my birth gender.

I had a wonderful time at Fantasia Fair and I am sure I would have a good time if I attended again, but weighing the cost versus the potential of growing more as a woman, I think my money would be better invested elsewhere.

A Connecticut sister hit the nail on the head. During one lunch, she distributed ballots to the Fantasia Fair attendees to vote for the Miss Cinderella Award. Another friend suggested that everyone vote for me, but my Connecticut sister remarked that the purpose of the award is to recognize the attendee who blossomed the most during the Fair and that I had blossomed before attending the Fair.

Nuf said!

[By the way, I attended Fantasia Fair three more times (2010, 2012 and 2014) for the same reason I attended Hamvention year after year: to see friends from all over the world, who I would not see otherwise.]

Source: Rue La La

Christopher Morley femulating on television’s Too Close For Comfort.